Acetic Acid → HCID 117995892, compound

HRID 1488305Notes

Reaction equation

HRID 1488305 reaction equation
[OH:1][C@H:2]1[C@H:7]([OH:8])[C@H:6]([OH:9])[C@H:5]([CH3:10])[O:4][C@H:3]1[O:11][CH2:12][CH2:13][NH:14][C:15]([C@@H:17]1[C@H:22]([C:23]([NH:25][CH2:26][CH2:27][O:28][C@H:29]2[C@@H:34]([OH:35])[C@H:33]([OH:36])[C@H:32]([OH:37])[C@H:31]([CH3:38])[O:30]2)=[O:24])[CH2:21][CH2:20][NH:19][CH2:18]1)=[O:16].O=[CH:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH2:48][C:49]1[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=1)=[O:46].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(O)(=O)C>C1COCC1.O>[OH:1][C@H:2]1[C@H:7]([OH:8])[C@H:6]([OH:9])[C@H:5]([CH3:10])[O:4][C@H:3]1[O:11][CH2:12][CH2:13][NH:14][C:15]([C@@H:17]1[C@H:22]([C:23](=[O:24])[NH:25][CH2:26][CH2:27][O:28][C@H:29]2[C@@H:34]([OH:35])[C@H:33]([OH:36])[C@H:32]([OH:37])[C@H:31]([CH3:38])[O:30]2)[CH2:21][CH2:20][N:19]([CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][C:45]([O:47][CH2:48][C:49]2[CH:54]=[CH:53][CH:52]=[CH:51][CH:50]=2)=[O:46])[CH2:18]1)=[O:16]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 5049666Sodium triacetoxyborohydrideHCID 18356473HCID 18356473, compoundHCID 117995795HCID 117995795, compound

Product 1

HCID 117995892HCID 117995892, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

(3R,4R)—N3,N4-bis(2-(((2R,3S,4R,5S,6S)-3,4,5-trihydroxy-6-methyltetrahydro-2H-pyran-2-yl)oxy)ethyl)piperidine-3,4-dicarboxamide (118 mg, 0.214 mmol) was dissolved in THF (2 mL), to which benzyl 6-oxohexanoate (70.7 mg, 0.321 mmol) in THF (0.5 mL) was added, followed by sodium triacetoxyborohydride (136 mg, 0.642 mmol) and acetic acid (3.67 μL, 0.064 mmol) were added, and the mixture was stirred at room temperature for 3 h. The product was isolated by preparative reverse-phase chromatography on C-18 column, using a gradient of 0-30% of AcN in water. UPLC Method F: m/e=756.4241 [M+1]; Rt=3.05 min

Workup

  1. additionwas added
  2. additionwere added
  3. customThe product was isolated by preparative reverse-phase chromatography on C-18 column

Sources & evidence

ORD record
ord-b383773db98143d0ba3a1b10e9eadab5
Source dataset
uspto-grants-2016_08
Patent number
US09427475B2

Reaction notes

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